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The third episode of Chappelle’s Show is a fairly representative episode from the show’s early period. I don’t want to try and compare installments of the show to works in a painter’s oeuvre, but there you have it. You take the good, you take the bad, you take them both and there you have an early-era Chappelle’s Show. In many ways, the show is stuck between trying variations on existing sketch comedy and trying to subvert those forms and produce something new and original.

The first two segments sit firmly in the first camp. The opening QVC-centric sketch centers on the program’s persistent focus on bodily humor. Far be it for me to say I’m above jokes concerning snot and genital herpes; there’s not a lot to say about this opening salvo other than this: If you like visual punchlines involving female pubic hair, this sketch is your freakin’ jam. The rest of us are be over here waiting for this one-note bit to end.

The “fake blooper” genre is likewise another staple within televised sketch comedy, but substituting Roots for the typical fare displayed on something like Dick Clark’s TV Bloopers And Practical Jokes gives this iteration some slight heft. But only slight. Whereas Chappelle’s Show at its best takes a stale premise and really runs with it to places of phenomenal creativity, the extras on this faux 25th-anniversary DVD don’t go nearly far enough with what is a potent premise. There’s certainly something to be done with one of the most powerful pieces of television ever produced. I’m just not sure “peeing babies” is one of those things. The only time this sketch comes close to something interesting comes when Dave Chappelle, in the Levar Burton/Kunta Kinte role, pretends to attack the actor whipping him during one of the miniseries’ iconic scenes. There’s a half-second in which the danger feels absolutely real, just before Chappelle releases the tension. But that half-second is pretty amazing, as the fear in the white actor’s eyes is absolutely real. But rather than exploit that moment, the sketch quickly dismisses it and moves on.

The other two segments in this episode are luckily far more successful. “Dave Chappelle’s It’s A Wonderful Chest” isn’t any less sophomoric than the QVC sketch in terms of the topic at hand: a woman’s enormous breasts. But there’s a real structure in play that moves this past a series of increasingly vivid descriptions of Sheila’s chest, one augmented on the segment’s real target: the way in which people treat one another differently based on appearance. This isn’t a “One To Grow On” treatment by any stretch of the imagination, but a series of comic vignettes in which Sheila realizes people are being nice to her curves rather than her personality. “It’s A Wonderful Chest” falls apart at the end, when it’s revealed Chappelle’s “angel” is really a janitor on PCP. But Lord knows Saturday Night Live shouldn’t hold the single patent on failing to end a sketch with a strong premise.

While “It’s a Wonderful Chest” ends the show, I found the penultimate sketch “Zapped!” to be the most successful. In some ways, it’s another cultural time capsule of a segment, one based not only on The Jamie Kennedy Experiment but also The WB’s entire promotional strategy, which featured its talent hamming it up in front of the network’s logo. But in other ways, it’s an eerily prescient sketch, one that foreshadows the way in which reality television got darker and crueler as each new show strove to outdo the last. In “Zapped!”, Chappelle convinces two small children their parents have died, breaks up a marriage through a staged sex scene with a man’s wife, and then ends up causing multiple deaths through a fake bank robbery. But what makes this a merely good sketch into a great one is the way in which he portrays Michigan J. Frog as a minstrel at the end of the pre-produced materials. It gets an audible shocked groan from the audience, one Chappelle is only happy to exploit in-studio after the video ends. His take on Michigan’s typical ragtime song (“I like chicken! Welcome back, niggers, to The WB!”) is impromptu, hysterical, and points the way to the type of comedy Chappelle’s Show would soon produce on a consistent basis.

“Episode 1-4” (season 1, episode 4; originally aired 2/12/2003)

The fourth installment continues with the show’s pattern sprinkling in some fun, if inconsequential, short sketches into a longer, more substantive piece. I don’t want to compare the show to Louie, since the two shows operate on completely different frequencies and serve separate comedic agendas. But I do enjoy both shows for at least one similar reason: Each time you experience an episode, you’re never quite sure what you’re about to see. The tone, form, and goals change on a weekly basis, even if they all stem from the same sensibility.

On the short side, we have two commercial parodies that both center around Chappelle’s sex life. The first one, based on a series of Apple “Switch” ads, features Chappelle extolling the crystal clear images on the Mac screens for helping his Internet porn habit reach the next level. (You can see an example of such an ad, one directly referenced inside the sketch, here. I almost wish Chappelle’s Show had been still around for the Mac/PC debacle, since the idea of him facing off against John Hodgman is sort of mind-blowing.) The second parody takes aim at the “Truth.com” ads, which sought to pull the curtain back (literally) on the ill effects of tobacco. In this case, pulling back the curtain reveals Chappelle in bed enjoying a post-coital smoke. That’s one to grow on!

As the first sketch that features Chappelle interacting with non-actors, “New York Boobs” isn’t exactly a groundbreaking sketch. But it does show how quick the man is on his feet, somehow placing blue ribbons upon women extolling the virtues of their chests without getting repeatedly slapped. Part of it has to do with his in-sketch persona, Lyle. Lyle wears an obviously fake mustache and talks in a manner that’s cultured, feminine, but above all else simply weird. What seems like a cheap gag meant to ogle the female body actually has a fairly important function, however. Above all, Chappelle is seeking to open up a space in which compliments don’t have to insinuate predatory desires.

He does this in an utterly ridiculous way, but the utter ridiculousness is also a statement of how far he has to couch his compliment in order to not make it seem threatening. As per usual on the show, neither side gets off without some sort of recrimination. On the one hand, Chappelle wants to demonstrate how some women go to great lengths to look attractive only to be offended anytime someone points out their efforts (“They’ll put them in your face, but it’s like, ‘Don’t talk about ’em!’” he says during his intro.) On the other hand, women have a strong reason for reacting this way: After all, men are generally not very… gentlemanly when offering up their praise. As strong as Chappelle’s Show is on racial issues, it’s can also be as astute when discussing relationships between the sexes. “New York Boobs” is a silly sketch, but it’s also one of many in the program that presents a topic often left unspoken and gives it voice.

I don’t particularly know how to segue from breast to reparations—then again, I’m not Dave Chappelle, who moves between the two in a two-part segment that essentially bookends the episode. The inspiration for the sketch comes from a real-life appearance on Donahue (shown in-episode) in which Caucasian males bemoaned the perceived rise of Affirmative Action in America. Rather than try and calmly (or angrily) express his opinion at the time, Chappelle left the show and took the fears of those men to the extreme, applying them to reparations for slavery. But rather than turn that idea into a comedic meditation on an African-American-controlled country, Chappelle instead paints a picture of a world in which the black community would quickly undo itself when presented with massive influxes of cash. Liquor stores get raided, cigarette trucks get purchased, and a man named Tron surpasses Bill Gates’ wealth through a lucky series of dice games.

All of this is chronicled through Chappelle playing multiple parts, most noticeably news anchor Chuck Taylor. Chappelle portrays Taylor in whiteface, and there’s an audible gasp when he first appears. Whether or not this is as offensive as, say, Ted Danson showing up at the Friar’s Club in blackface is a matter of taste. Since Chappelle is such an equal-opportunity offender, it doesn’t seem particularly worthy of ire. But mileage will vary, as with most things related to this show. Just as “New York Boobs” buries centuries of male-female interactions in its subtext, the reparation segments are as much about the economic realities of blue-collar African-Americans as it is a desire to have the country atone for its horrific past. “I don’t like to be forced!” cries out a white male in the Donahue crowd. “Oh, you mean like slavery forced?” Chappelle rhetorically replies in his own studio. In both of this episode’s central sketches, Chappelle’s Show explores just how far we haven’t come, even in the 21st century. The fact that a sketch-comedy show is one of the few ways we might be able to advance the dialogue, and thus ourselves, is both fascinating as well as sobering.

Stray observations:

The way Chappelle talks about obsessively collecting DVDs is almost quaint. And we’re only 10 years out from the initial airings of this episodes! Our children will one day mock our need for physical media one day. Or, at the current speed of technological advancement, that day may come in 2013, assuming the Mayans were wrong.

I love the idea that the only thing between us and the apocalypse is a pair of breasts. Maybe that’s the plot of NBC’s upcoming show Revolution and we just don’t know it yet.

I contemplated putting a series of quotes here in the observations each week, but you all did a great job last week in the comments of doing that anyways. I won’t spoil the fun.

The line “I’m rich, beeyotch!” that plays over Chappelle’s production logo comes from the reparations sketch, uttered by actor Donnell Rawlings.

At one point during “New York Boobs,” Chappelle praises a women’s chest right in front of her father. Holy awkward, Batman. Somehow, Chappelle makes it seem like an even nobler gesture, praising this man’s genetic contributions to his offspring.

While the first half of the reparations sketch features plenty of varied locations, the latter half essentially plays like a “Weekend Update” segment on Saturday Night Live, and suffers a bit by comparison.

Next week: Paul Mooney and Charlie Murphy make their first appearances on the show.